RU2008151888A - SUBSTITUTED ARILPIPERIDINYLALKINYLADENOSINES AS A2AR AGONISTS - Google Patents

SUBSTITUTED ARILPIPERIDINYLALKINYLADENOSINES AS A2AR AGONISTS Download PDF

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RU2008151888A
RU2008151888A RU2008151888/04A RU2008151888A RU2008151888A RU 2008151888 A RU2008151888 A RU 2008151888A RU 2008151888/04 A RU2008151888/04 A RU 2008151888/04A RU 2008151888 A RU2008151888 A RU 2008151888A RU 2008151888 A RU2008151888 A RU 2008151888A
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Джейсон М. РИГЕР (US)
Джейсон М. Ригер
Роберт Д. ТОМПСОН (US)
Роберт Д. Томпсон
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Аденозин Терапеутикс, ЭлЭлСи (US)
Аденозин Терапеутикс, ЭлЭлСи
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Abstract

1. Соединение формулы (I) или его фармацевтически приемлемая соль: ! ! где R1 и R2 независимо выбраны из группы, состоящей из Н, (С1-С8)алкила, (С3-С8)циклоалкила, (С3-С8)циклоалкил(С1-С8)алкилена, арила, арил(С1-С8)алкилена, гетероарила, группы гетероарил(С1-С8)алкилен-, диарил(С1-С8)алкилена и дигетероарил(С1-С8)алкилена, где арильные и гетероарильные кольца возможно замещены 1-4 группами, независимо выбранными из фторо, хлоро, иодо, бромо, метила, трифторметила и метокси; ! каждый R независимо выбран из группы, состоящей из Н, С1-С4алкила, циклопропила, циклобутила и (СН2)ациклопропила; !Х представляет собой СН или N, при условии, что когда Х представляет собой СН, тогда Z не может быть замещен галогеном, С1-С6алкилом, гидроксилом, амино или моно- или ди-(С1-С6алкил)амино; ! Y выбран из группы, состоящей из О, NR1, -(OCH2CH2O)mCH2- и -(NR1CH2CH2O)mCH2-, при условии, что когда Y представляет собой О или NR1, тогда имеется по меньшей мере один заместитель по Z; ! Z выбран из группы, состоящей из 5-членного гетероарила, 6-членного арила, 6-членного гетероарила, карбоциклического биарила и гетероциклического биарила, где точка присоединения Y к Z представляет собой атом углерода в Z, где Z замещен 0-4 группами, независимо выбранными из группы, состоящей из F, Cl, Вr, I, (С1-С4)алкила, -(CH2)aOR3, -(CH2)aNR3R3, -NHOH, -NR3NR3R3, нитро, -(CH2)aCN, -(CH2)aCO2R3, -(CH2)aCONR3R3, трифторметила и трифторметокси; ! альтернативно, Y и Z вместе образуют группировку индолил, индолинил, изоиндолинил, тетрагидроизохинолинил или тетрагидрохинолинил, где точкой присоединения является кольцевой атом азота, и где указанная группировка индолил, индолинил, изоиндолинил, тетрагидроизохинолинил или тетрагидрохинолинил замещена 0-4 группами, 1. The compound of formula (I) or its pharmaceutically acceptable salt:! ! where R1 and R2 are independently selected from the group consisting of H, (C1-C8) alkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkyl (C1-C8) alkylene, aryl, aryl (C1-C8) alkylene, heteroaryl groups heteroaryl (C1-C8) alkylene-, diaryl (C1-C8) alkylene and diheteroaryl (C1-C8) alkylene, where aryl and heteroaryl rings are optionally substituted with 1-4 groups independently selected from fluoro, chloro, iodo, bromo methyl, trifluoromethyl and methoxy; ! each R is independently selected from the group consisting of H, C1-C4 alkyl, cyclopropyl, cyclobutyl and (CH2) acyclopropyl; ! X represents CH or N, provided that when X represents CH, then Z cannot be substituted with halogen, C1-C6 alkyl, hydroxyl, amino or mono- or di- (C1-C6 alkyl) amino; ! Y is selected from the group consisting of O, NR1, - (OCH2CH2O) mCH2 - and - (NR1CH2CH2O) mCH2-, provided that when Y is O or NR1, then there is at least one Z substituent; ! Z is selected from the group consisting of 5-membered heteroaryl, 6-membered aryl, 6-membered heteroaryl, carbocyclic biaryl and heterocyclic biaryl, where the point of attachment of Y to Z represents a carbon atom in Z, where Z is substituted with 0-4 groups, independently selected from the group consisting of F, Cl, Br, I, (C1-C4) alkyl, - (CH2) aOR3, - (CH2) aNR3R3, -NHOH, -NR3NR3R3, nitro, - (CH2) aCN, - (CH2 ) aCO2R3, - (CH2) aCONR3R3, trifluoromethyl and trifluoromethoxy; ! alternatively, Y and Z together form an indolyl, indolinyl, isoindolinyl, tetrahydroisoquinolinyl or tetrahydroquinolinyl group, where the attachment point is a ring nitrogen atom, and where the indicated group is indolyl, indolinyl, isoindolinyl, tetrahydroisoquinolinyl, or tetrahydroquinolino, tetrahydroquinoline 0,

Claims (11)

1. Соединение формулы (I) или его фармацевтически приемлемая соль:1. The compound of formula (I) or its pharmaceutically acceptable salt:
Figure 00000001
Figure 00000001
 где R1 и R2 независимо выбраны из группы, состоящей из Н, (С1-С8)алкила, (С3-С8)циклоалкила, (С3-С8)циклоалкил(С1-С8)алкилена, арила, арил(С1-С8)алкилена, гетероарила, группы гетероарил(С1-С8)алкилен-, диарил(С1-С8)алкилена и дигетероарил(С1-С8)алкилена, где арильные и гетероарильные кольца возможно замещены 1-4 группами, независимо выбранными из фторо, хлоро, иодо, бромо, метила, трифторметила и метокси;where R 1 and R 2 are independently selected from the group consisting of H, (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkylene, aryl, aryl (C 1 -C 8 ) alkylene, heteroaryl groups heteroaryl (C 1 -C 8 ) alkylene, diaryl (C 1 -C 8 ) alkylene and diheteroaryl (C 1 -C 8 ) alkylene, where aryl and heteroaryl the rings are optionally substituted with 1-4 groups independently selected from fluoro, chloro, iodo, bromo, methyl, trifluoromethyl and methoxy; каждый R независимо выбран из группы, состоящей из Н, С1-С4алкила, циклопропила, циклобутила и (СН2)ациклопропила;each R is independently selected from the group consisting of H, C 1 -C 4 alkyl, cyclopropyl, cyclobutyl and (CH 2 ) a cyclopropyl; Х представляет собой СН или N, при условии, что когда Х представляет собой СН, тогда Z не может быть замещен галогеном, С1-С6алкилом, гидроксилом, амино или моно- или ди-(С1-С6алкил)амино;X represents CH or N, provided that when X represents CH, then Z cannot be substituted with halogen, C 1 -C 6 alkyl, hydroxyl, amino or mono- or di- (C 1 -C 6 alkyl) amino ; Y выбран из группы, состоящей из О, NR1, -(OCH2CH2O)mCH2- и -(NR1CH2CH2O)mCH2-, при условии, что когда Y представляет собой О или NR1, тогда имеется по меньшей мере один заместитель по Z;Y is selected from the group consisting of O, NR 1 , - (OCH 2 CH 2 O) m CH 2 - and - (NR 1 CH 2 CH 2 O) m CH 2 -, provided that when Y is O or NR 1 , then there is at least one Z substituent; Z выбран из группы, состоящей из 5-членного гетероарила, 6-членного арила, 6-членного гетероарила, карбоциклического биарила и гетероциклического биарила, где точка присоединения Y к Z представляет собой атом углерода в Z, где Z замещен 0-4 группами, независимо выбранными из группы, состоящей из F, Cl, Вr, I, (С1-С4)алкила, -(CH2)aOR3, -(CH2)aNR3R3, -NHOH, -NR3NR3R3, нитро, -(CH2)aCN, -(CH2)aCO2R3, -(CH2)aCONR3R3, трифторметила и трифторметокси;Z is selected from the group consisting of 5-membered heteroaryl, 6-membered aryl, 6-membered heteroaryl, carbocyclic biaryl and heterocyclic biaryl, where the point of attachment of Y to Z represents a carbon atom in Z, where Z is substituted with 0-4 groups, independently selected from the group consisting of F, Cl, Br, I, (C 1 -C 4 ) alkyl, - (CH 2 ) a OR 3 , - (CH 2 ) a NR 3 R 3 , -NHOH, -NR 3 NR 3 R 3 , nitro, - (CH 2 ) a CN, - (CH 2 ) a CO 2 R 3 , - (CH 2 ) a CONR 3 R 3 , trifluoromethyl and trifluoromethoxy; альтернативно, Y и Z вместе образуют группировку индолил, индолинил, изоиндолинил, тетрагидроизохинолинил или тетрагидрохинолинил, где точкой присоединения является кольцевой атом азота, и где указанная группировка индолил, индолинил, изоиндолинил, тетрагидроизохинолинил или тетрагидрохинолинил замещена 0-4 группами, независимо выбранными из группы, состоящей из F, Cl, Вr, I, С1-C4алкила, -(CH2)aOR3, -(CH2)aNR3R3, -NHOH, -NR3NR3R3, NO2, -(СН2)аСN, -(CH2)aCO2R3, -(CH2)aCONR3R3, СF3 и ОСF3;alternatively, Y and Z together form an indolyl, indolinyl, isoindolinyl, tetrahydroisoquinolinyl or tetrahydroquinolinyl group, where the point of attachment is a ring nitrogen atom, and where said indolyl, indolinyl, isoindolinyl, tetrahydroisoquinolinyl, tetrahydroquinolino group, independently selected tetrahydroquinoline group consisting of F, Cl, Br, I, C 1 -C 4 alkyl, - (CH 2 ) a OR 3 , - (CH 2 ) a NR 3 R 3 , -NHOH, -NR 3 NR 3 R 3 , NO 2 , - (CH 2 ) a CN, - (CH 2 ) a CO 2 R 3 , - (CH 2 ) a CONR 3 R 3 , CF 3 and OCF 3 ; R3 независимо выбран из группы, состоящей из Н, (С1-С6)алкила, циклоалкила, арила и гетероарила;R 3 is independently selected from the group consisting of H, (C 1 -C 6 ) alkyl, cycloalkyl, aryl, and heteroaryl; R4 выбран из группы, состоящей из CH2OR, C(O)NRR и CO2R;R 4 selected from the group consisting of CH 2 OR, C (O) NRR and CO 2 R; R5 выбран из группы, состоящей из СН2СН2, СН=СН и С=С;R 5 is selected from the group consisting of CH 2 CH 2 , CH = CH and C = C; а выбран из 0, 1 и 2;and selected from 0, 1 and 2; m выбран из 1, 2 и 3;m is selected from 1, 2, and 3; n выбран из 0, 1 и 2;n is selected from 0, 1 and 2; каждый р независимо выбран из 0, 1 и 2; иeach p is independently selected from 0, 1, and 2; and q выбран из 0, 1 и 2.q is selected from 0, 1 and 2. 2. Соединение по п.1, представляющее собой соединение формулы (Ia) или его фармацевтически приемлемую соль:2. The compound according to claim 1, which is a compound of formula (Ia) or its pharmaceutically acceptable salt:
Figure 00000002
Figure 00000002
 3. Соединение по п.2, представляющее собой соединение формулы (Ib) или его фармацевтически приемлемую соль:3. The compound according to claim 2, which is a compound of formula (Ib) or its pharmaceutically acceptable salt:
Figure 00000003
Figure 00000003
 где каждый Z' независимо выбран из группы, состоящей из F, Cl, Br, I, C1-С4алкила, -(CH2)aOR3, -(CH2)aNR3R3, -NHOH, -NR3NR3R3, NO2, -(CH2)aCN, -(CH2)aCO2R3, -(CH2)aCONR3R3, СF3 и ОСF3.where each Z 'is independently selected from the group consisting of F, Cl, Br, I, C 1 -C 4 alkyl, - (CH 2 ) a OR 3 , - (CH 2 ) a NR 3 R 3 , -NHOH, - NR 3 NR 3 R 3 , NO 2 , - (CH 2 ) a CN, - (CH 2 ) a CO 2 R 3 , - (CH 2 ) a CONR 3 R 3 , CF 3 and OCF 3 . 4. Соединение по п.3, где R выбран из Н, метила, этила или циклопропила.4. The compound according to claim 3, where R is selected from H, methyl, ethyl or cyclopropyl. 5. Соединение по п.3, представляющее собой соединение формулы (Ic) или его фармацевтически приемлемую соль:5. The compound according to claim 3, which is a compound of formula (Ic) or its pharmaceutically acceptable salt:
Figure 00000004
Figure 00000004
 6. Соединение по п.5, где Z' выбран из группы, состоящей из F, Cl, метила, OR3, NO2, CN, NR3R3 и CO2R3.6. The compound according to claim 5, where Z 'is selected from the group consisting of F, Cl, methyl, OR 3 , NO 2 , CN, NR 3 R 3 and CO 2 R 3 . 7. Соединение по п.5, где R3 представляет собой метил или водород.7. The compound according to claim 5, where R 3 represents methyl or hydrogen. 8. Соединение по п.1, выбранное из группы, состоящей из соединений под номерами 3, 5-31 и 33-57, представленных в Таблице 1.8. The compound according to claim 1, selected from the group consisting of compounds numbered 3, 5-31 and 33-57, shown in Table 1. 9. Фармацевтическая композиция, содержащая соединение по любому из пп.1-8 и фармацевтически приемлемый носитель.9. A pharmaceutical composition comprising a compound according to any one of claims 1 to 8 and a pharmaceutically acceptable carrier. 10. Соединение по любому из пп.1-8 для применения в терапии.10. The compound according to any one of claims 1 to 8 for use in therapy. 11. Применение соединения по любому из пп.1-8 в производстве лекарственного средства для лечения заболевания, связанного с А2А-рецепторами. 11. The use of a compound according to any one of claims 1 to 8 in the manufacture of a medicament for the treatment of a disease associated with A 2A receptors.
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